2-Bromopropane → 3-Methyl-2-phenylbutanoic acid

HRID 638106Notes

Reaction equation

HRID 638106 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:12](Br)([CH3:14])[CH3:13].S([C:20]1[CH:26]=CC(C)=C[CH:21]=1)([O-])(=O)=O.C[N+](C)(C)C.[Cl-].[NH4+]>CN(C)C=O>[CH:12]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:14])[CH3:13].[CH:20]([CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([OH:10])=[O:9])([CH3:26])[CH3:21]

Participants

7

Reactant 4

HCID 63582-BromopropaneHCID 7559Methyl phenylacetate2×HCID 25517Ammonium ChlorideHCID 6451622Tetramethylammonium toluene-p-sulphonate

Product 2

HCID 190243-Methyl-2-phenylbutanoic acidHCID 5051294Methyl 3-methyl-2-phenylbutanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into the cathode chamber of an electrolytic cell divided with a diaphragm (asbestos) was placed a solution of 10 mmols of methyl phenylacetate, 12 mmols of isopropyl bromide and 1.0 g of tetramethylammonium tosylate in 30 ml of anhydrous dimethylformamide. Constant current electrolysis was conducted at 0.2 A/cm2 with use of lead for the anode and carbon for the cathode. After passing 1.5 F of electricity per mol of the methyl phenylacetate at 20° to 25° C., the cathode solution was added to a saturated aqueous solution of ammonium chloride and the mixture was extracted twice with ether. The ether was distilled off and the residue was purified by silica gel column chromatography using hexane-ethyl acetate (10:1), giving methyl α-isopropylphenylacetate in a yield of 80% and α-isopropylphenylacetic acid in a yield of 9%. The spectral data of the ester were as follows.

Workup

  1. customat 20° to 25° C.
  2. extractionthe mixture was extracted twice with ether
  3. distillationThe ether was distilled off
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c80f653cfc7c40fe86df095ca30fad9e
Source dataset
uspto-grants-1985_12
Patent number
US04560447

Reaction notes

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